JP5561929B2 - 新規有機化合物 - Google Patents
新規有機化合物 Download PDFInfo
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- JP5561929B2 JP5561929B2 JP2008324469A JP2008324469A JP5561929B2 JP 5561929 B2 JP5561929 B2 JP 5561929B2 JP 2008324469 A JP2008324469 A JP 2008324469A JP 2008324469 A JP2008324469 A JP 2008324469A JP 5561929 B2 JP5561929 B2 JP 5561929B2
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Description
下記一般式(1)に示される有機化合物を提供する。
前記アルキル基、前記アルコシキ基、前記アミノ基、前記アリール基、前記複素環基は置換基を有してもよく、前記置換基は、アルキル基、アラルキル基、アリール基、複素環基、アミノ基、アルコキシル基、シアノ基、ハロゲン原子から選ばれる。
メチル基、エチル基、プロピル基などのアルキル基、
ベンジル基などのアラルキル基、
フェニル基、ビフェニル基などのアリール基、
ピリジル基、ピロリル基などの複素環基、
ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基などのアミノ基、
メトキシル基、エトキシル基、プロポキシル基、フェノキシル基などのアルコキシル基、
シアノ基、フッ素、塩素、臭素、ヨウ素などのハロゲン原子などが挙げられるが、もちろんこれらに限定されるものではない。
そのためには
1つ目に振動子強度が高いこと
2.つ目に発光にかかわる骨格の振動部分が少ないこと
があげられる。これら2点の特性が同時に求められる。
1.発光層内での電子・ホールの輸送。
2.ホスト材料の励起子生成。
3.ホスト材料同士の分子間の励起エネルギー伝達。
4.ホスト材料からゲスト材料への励起エネルギー移動。
を二硫化炭素500ml中に−40℃下で混合し、3時間攪拌を行った。そのまま室温まで戻し、1時間攪拌を行った後、水中にあけて析出物のろ過を行い、エタノール洗浄を行った後、乾燥後、黄土色の固体E3を20g(収率:85%)得た。このE3 11.6g(50mmol)、E4 10.5g(50mmol)をエタノール200ml中に入れ、60度まで加熱した後、5M水酸化ナトリウム水溶液20mlを滴下した。滴下終了後80度に加熱して2時間攪拌した後冷却後、析出物のろ過を行い、水、エタノールで洗浄した後、80℃で減圧加熱乾燥を行い濃緑色の固体E5を18.2g(収率:95%)得た。
例示化合物A2の、1×10−5mol/lにおけるトルエン溶液の発光スペクトルは、日立製F−4500を用いて、350nmの励起波長においてフォトルミネッセンスの測定を行った結果、457nmに最大強度を有するスペクトルであった。
比較例として化合物F1、F2を合成してフォトルミネッセンス、吸収スペクトルの測定を元に量子収率の比較を行った。吸収スペクトルは日本分光製 UV−570を用いた。量子収率は例示化合物A2を1.0として相対的な強度を出した。
[例示化合物A6の合成]
実施例1で用いられる有機化合物E4をE10に変更した以外は実施例1と同様の反応、精製を行った。
本実施例では、多層型有機発光素子の第五の例で示した素子(陽極/ホール注入層/ホール輸送層/発光層/ホール・エキシトンブロッキング層/電子輸送層/陰極)とした。ガラス基板上に100nmのITOをパターニングした。そのITO基板上に、以下の有機層と電極層を10−5Paの真空チャンバー内で抵抗加熱による真空蒸着して連続製膜し、対向する電極面積が3mm2になるようにした。
ホール輸送層(30nm) G−1
発光層(30nm) ホストG−2、ゲスト:例示化合物 (重量比 5%)
ホール・エキシトンブロッキング層(10nm) G−3
電子輸送層(30nm) G−4
金属電極層1(1nm) LiF
金属電極層2(100nm) Al
実施例3乃至実施例19の発光効率と電圧を下表に示す
本発明に係わる有機化合物は高い量子収率と青に適した発光を有する新規化合物であり、有機発光素子に用いた場合、良好な発光特性を有する発光素子を作ることができる。
2,15 画素回路
11 走査信号ドライバー
12 情報信号ドライバー
13 電流供給源
14 画素
21 第一の薄膜トランジスタ(TFT)
22 コンデンサー(Cadd)
23 第二の薄膜トランジスタ(TFT)
31 基板
32 防湿層
33 ゲート電極
34 ゲート絶縁膜
35 半導体膜
36 ドレイン電極
37 ソース電極
38 TFT素子
39 絶縁膜
310 コンタクトホール(スルーホール)
311 陽極
312 有機層
313 陰極
314 第一の保護層
315 第二の保護層
Claims (10)
- R 1 、R 2 、R 9 、R 10 はそれぞれ独立に前記水素原子、前記アルキル基、前記アリール基のいずれかであることを特徴とする請求項1に記載の有機化合物。
- R 1 、R 2 、R 9 、R 10 がそれぞれ独立に前記アルキル基である場合、前記アルキル基はイソプロピル基であり、R 1 、R 2 、R 9 、R 10 がそれぞれ独立に前記アリール基である場合、前記アリール基はフェニル基、ビフェニル基、ナフチル基のいずれかであり、
前記置換基としての前記アルキル基は、ターシャリブチル基であることを特徴とする請求項2に記載の有機化合物。 - R 3 乃至R 8 、R 11 乃至R 18 はそれぞれ独立に前記水素原子、前記アルキル基、前記アリール基のいずれかであることを特徴とする請求項1乃至3のいずれか一項に記載の有機化合物。
- 陽極と陰極と前記陽極と前記陰極の間に配置される有機化合物層とを有する有機発光素子において、
前記有機化合物層は請求項1乃至4のいずれか一項に記載の有機化合物を有することを特徴とする有機発光素子。 - 前記有機化合物層は発光層であることを特徴とする請求項5に記載の有機発光素子。
- 感光体と前記感光体へ潜像を露光する光源を有する電子写真方式の画像形成装置において、
前記光源は請求項5あるいは6に記載の有機発光素子を複数有することを特徴とする電子写真方式の画像形成装置。 - 照明装置であって、
前記照明装置は請求項5あるいは6に記載の有機発光素子を複数面内に有することを特徴とする照明装置。 - 画素と、画素回路と、情報信号線と、電流供給線を有する表示装置であって、
前記画素は請求項5あるいは6に記載の有機発光素子を有することを特徴とする表示装置。 - 基板と、請求項5あるいは6に記載の有機発光素子と、カラーフィルタを有することを特徴とする装置。
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008324469A JP5561929B2 (ja) | 2008-12-19 | 2008-12-19 | 新規有機化合物 |
PCT/JP2009/071365 WO2010071223A1 (en) | 2008-12-19 | 2009-12-16 | Novel organic compound |
KR1020117016008A KR101312330B1 (ko) | 2008-12-19 | 2009-12-16 | 신규 유기 화합물 |
CN200980150000.7A CN102245545B (zh) | 2008-12-19 | 2009-12-16 | 有机化合物 |
EP09833524.3A EP2379472B1 (en) | 2008-12-19 | 2009-12-16 | Novel organic compound |
US13/140,804 US8431711B2 (en) | 2008-12-19 | 2009-12-16 | Organic compound |
US13/850,216 US8963416B2 (en) | 2008-12-19 | 2013-03-25 | Organic compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008324469A JP5561929B2 (ja) | 2008-12-19 | 2008-12-19 | 新規有機化合物 |
Publications (2)
Publication Number | Publication Date |
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JP2010143880A JP2010143880A (ja) | 2010-07-01 |
JP5561929B2 true JP5561929B2 (ja) | 2014-07-30 |
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Application Number | Title | Priority Date | Filing Date |
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JP2008324469A Active JP5561929B2 (ja) | 2008-12-19 | 2008-12-19 | 新規有機化合物 |
Country Status (6)
Country | Link |
---|---|
US (2) | US8431711B2 (ja) |
EP (1) | EP2379472B1 (ja) |
JP (1) | JP5561929B2 (ja) |
KR (1) | KR101312330B1 (ja) |
CN (1) | CN102245545B (ja) |
WO (1) | WO2010071223A1 (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5561929B2 (ja) * | 2008-12-19 | 2014-07-30 | キヤノン株式会社 | 新規有機化合物 |
JP5424635B2 (ja) | 2008-12-19 | 2014-02-26 | キヤノン株式会社 | ジアセナフト[1,2−b:1’,2’−k]クリセン誘導体 |
JP5495665B2 (ja) * | 2009-08-10 | 2014-05-21 | キヤノン株式会社 | 有機化合物及びこれを用いた有機発光素子 |
JP4721475B2 (ja) * | 2009-10-01 | 2011-07-13 | キヤノン株式会社 | ジインデノピセン化合物及びこれを使用した有機発光素子 |
JP5700952B2 (ja) * | 2010-04-30 | 2015-04-15 | キヤノン株式会社 | 新規有機化合物およびそれを有する有機発光素子 |
JP5618647B2 (ja) * | 2010-06-18 | 2014-11-05 | キヤノン株式会社 | 新規有機化合物およびそれを有する有機発光素子 |
JP6084001B2 (ja) * | 2011-12-06 | 2017-02-22 | キヤノン株式会社 | 新規有機化合物、有機発光素子及び画像表示装置 |
JP6132580B2 (ja) | 2013-02-15 | 2017-05-24 | キヤノン株式会社 | 新規縮合多環化合物およびそれを有する有機発光素子 |
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US20130216268A1 (en) | 2013-08-22 |
WO2010071223A1 (en) | 2010-06-24 |
CN102245545B (zh) | 2014-06-04 |
EP2379472A4 (en) | 2013-01-23 |
EP2379472A1 (en) | 2011-10-26 |
JP2010143880A (ja) | 2010-07-01 |
US8963416B2 (en) | 2015-02-24 |
US20110251394A1 (en) | 2011-10-13 |
CN102245545A (zh) | 2011-11-16 |
US8431711B2 (en) | 2013-04-30 |
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